Answers

D3D cbuffer resources must be sized as a multiple of 16 bytes (fundamentally a cbuffer is a collection of constants, each of which is composed of 4 four byte elements). The "uint someCBufferSize = (sizeof(SomeCBuffer) + 15) / 16 * 16;" logic
takes advantage of integer division truncation to ensure that the resulting value is a multiple of 16 and contains the minimum number of bytes necessary to contain all the data without any excess bytes being wasted.

If your CPU-side struct representation of the GPU-side cbuffer happens to be a multiple of 16, then you could leave off this logic as it would be superfluous. But if the struct ever changed such that it was no longer a multiple of 16 then you would wind
up with bad things happening (how bad would probably depend on the graphics driver but it's possible that the D3D runtime itself would return a failure HRESULT without leaving it up to the graphics driver; I've never tried so I don't know).

Since cbuffer constants are also not supposed to straddle multiple 16 byte chunks*, I generally prefer to define my CPU-side structs using DirectX::XMFLOAT4 elements and DirectX::XMFLOAT4X4 elements. (*Matrices such as XMFLOAT4X4 are treated as
being made up of multiple 4 element constants, none of which individually straddles a 16 byte boundary, thus preserving the proper 16 byte alignment which the GPU registers require.) Defining them this way (and using the
register and
packoffset keywords in HLSL) results in fewer errors and oddities since the constant values are given explicit locations on the GPU and the data (assuming you comment the struct appropriately)
should always be placed properly on the CPU such that a call to ID3D11DeviceContext::UpdateSubresource will result in the correct data ending up in their proper places on the GPU-side.